Carbon tetrabromide → HCID 86620175, compound

HRID 1247679Notes

Reaction equation

HRID 1247679 reaction equation
BrC(Br)(Br)Br.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([I:17])=[CH:14][CH2:15]O)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)C(C)C)(C)C.[SH:46][C:47]1[CH:59]=[CH:58][C:50]([O:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])=[C:49]([CH3:60])[CH:48]=1>C(Cl)Cl>[Br:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[I:17])=[CH:14]/[CH2:15][S:46][C:47]2[CH:59]=[CH:58][C:50]([O:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])=[C:49]([CH3:60])[CH:48]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 86209014HCID 86209014, compound

Product 1

HCID 86620175HCID 86620175, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tetrabromomethane (2.1 g, 6.6 mmol) in dry methylene chloride (20 mL) was added dropwise to an ice-cooled solution of 3-(4-bromophenyl)-3-iodoprop-2-en-1-ol (1.5 g, 4.4 mmol) and triphenylphosphine (2.4 g, 9.0 mmol) in dry methylene chloride (50 mL). The reaction mixture was stirred at room temperature for 2 h and the solvent was evaporated in vacuo. Under nitrogen atmosphere, N,N-diisopropylethylamine (1.2 g, 9.0 mmol) and ethyl (4-mercapto-2-methylphenoxy)acetate (1.5 g, 6.6 mmol; Bioorg. Med. Chem. Lett. 2003, 13, 1517) were added to the residue. The reaction mixture was stirred for 3 h, filtered through a short path of silica gel and the filtrate was evaporated in vacuo. The residue was purified by column chromatography (silica gel Merck 60, hexane/ethyl acetate 1:0–9:1) giving 0.80 g of the ester. Yield: 0.80 g (40%).

Workup

  1. customthe solvent was evaporated in vacuo
  2. stirringThe reaction mixture was stirred for 3 h
  3. filtrationfiltered through a short path of silica gel
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography (silica gel Merck 60, hexane/ethyl acetate 1:0–9:1)

Sources & evidence

ORD record
ord-2cdf02f40bae4c469402c4a9496a9334
Source dataset
uspto-grants-2006_10
Patent number
US07129268B2

Reaction notes

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